1. Field of the Invention
This invention relates to novel substituted 4-oxo-3-quinolinecarboxylic acids, to methods for the preparation thereof, and compositions and methods for the use thereof as anitbacterial agents.
2. Information Disclosure Statement
Antibacterially active 4-oxo-3-quinolinecarboxylic acids are known in the prior art which includes the following references.
Lesher and Carabateas U.S. Pat. No. 3,753,993, issued Aug. 21, 1973, discloses 7-(2,6-dimethyl-4-pyridinyl)-1-ethyl-1,4-dihydro-4-oxo-3-quinolinecarboxyl ic acid.
Sterling Drug Inc. European Patent Application, published Apr. 30, 1986 under No. 179,239, discloses 7-(2,6-dimethyl-4-pyridinyl)-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolin ecarboxylic acid.
Hayakawa et al. U.S. Pat. No. 4,382,892, issued May 10, 1983, discloses 9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-pyrido[ 1,2,3-de][1,4]benzoxazine-6-carboxylic acid: ##STR2## also known under the generic name ofloxacin.
D. T. Chu U.S. Pat. No. 4,540,694, issued Sept. 10, 1985, discloses a genus of 1-pyridine-substituted quino-benzoxazines having the formula ##STR3## wherein X is halogen or hydrogen; R.sub.2 is a substituent; and R.sub.1 is hydrogen or a carboxy protecting group. The specification of the patent suggests substitution on the pyridine ring including alkyl groups but there are no specific examples thereof.
Gilligan et al. U.S. Pat. No. 4,636,506, issued Jan. 13, 1987, discloses a genus of compounds of the formula ##STR4## wherein
R.sub.1 is hydrogen, a pharmaceutically acceptable cation or alkyl of 1 to 3 carbon atoms;
Y is selected from the group consisting of alkyl and haloalkyl of 1 to 3 carbon atoms, alkyl, vinyl, cyclopropyl, hydroxyethyl, phenyl, 4-hydroxyphenyl and 4-fluorophenyl;
R.sub.2 is 3-pyridyl or 4-pyridyl which may be substituted by various groups not including alkyl;
R.sub.3 is fluoro; or R.sub.3 and Y may be combined to form a bridge of the formula --X(CH.sub.2).sub.n --CHR.sub.4 -- or --X--(CH.sub.2).sub.n --C(.dbd.CH.sub.2)-- wherein
X is CH.sub.2, O, S, NH or NCH.sub.3 ;
n is 0, 1 or2, and
R.sub.4 is selected from the group consisting of hydrogen, alkyl and halo alkyl of 1 to 3 carbon atoms, hydroxymethyl, hydroxyethyl, aminoethyl and phenyl.
The only specific compounds disclosed where R.sub.3 and Y are combined are Examples 7 and 8 which respectively have the following structures: ##STR5##